I’m standing in the long grass at the Yorktown Battlefield, surrounded by earthen mounds pockmarked with subtle indentations from where bullets and cannonballs pummeled them more than 240 years ago. Through the veil of pine trees, the battlefield drops precipitously into the York River, which feeds into the Chesapeake Bay. Where Lafayette was waiting, I think to myself, the Hamilton score playing in my head. But this isn’t a Broadway production — it’s a very real, very maintained site, home to the most significant turning point in the American Revolution.
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“I’m embarrassed I never made it to Yorktown before now,” I tell Celeste Gucanac, the owner of Mobjack Coffee Roasters in Historic Yorktown. She smiles understandingly, “When you’ve only got a day, you can’t do it all.” It’s a gracious admission, but she’s right. Like so many visitors to this part of Virginia, my childhood experience was limited to Williamsburg for school fieldtrips, plus Busch Gardens and Water Country USA for summertime day trips. However, the ways to discover and experience the Williamsburg area — Jamestown, Williamsburg, and Yorktown — require much more time than a day, and the ways to discover these places constantly evolve in tune with our nation’s own evolution.
So, whether you’ve visited this colonial corridor a dozen times or planning a first trip, here’s where to get started:
Begin your trip in “America’s birthplace,” where the first settlers arrived in 1607, more than a decade before the Mayflower.
“That’s our tagline for Jamestowne,” explains Angel Johnston. “All of these keystone moments happened here. The start of the country’s democratic government and the arrival of the first African people were here, right on the peninsula.”
Step into the 17th century church in Historic Jamestowne. Photography courtesy of Visit Williamsburg
The ways to discover this history are numerous and accessible at all levels. All ages will delight in entering the replicated structures and huts at Jamestown Settlement that simulate the homes of the English colonists who settled on this shore and the Powhatan indigenous Americans who lived here before them. Docked beside the English settlement are the life-size replica ships, Godspeed and Discovery.
Serious history buffs can live out their Indiana Jones fantasies at Historic Jamestowne, the physical site of the original James Fort and Jamestowne. Here, you can see an active archeological dig that’s uncovered more than four million artifacts since 1994. “A lot of people are surprised that we’re still working on uncovering the history of James Fort and Jamestowne. In the general public’s mind, they’ve never seen a site like this that’s continuing to discover incredible things about our past,” Johnston says.
Sip a glass of A Midsummer’s Night White as you explore the vineyards at Williamsburg Winery. Photography courtesy of Visit Williamsburg
Next, spend time sightseeing the land so central to the start of the nation. Located right on the James River, you can rent a kayak or paddleboard from Bay Country Kayaking and paddle around the shore and marsh. The 52-mile Virginia Capital Trail also makes Jamestown a destination for serious cyclists. This scenic route leads between the past and present state capitals (Jamestown and Richmond) and every mile is saturated with history. Reward yourself with a prosciutto and provolone baguette and cold beer from the cyclist-friendly Spoke & Art Provisions Co. If you prefer grapes over grain, head to Williamsburg Winery, where you can take a tour before concluding with a flight of petit verdot, viogner, and blanc de blanc sparkling wine while overlooking the vineyards.
Stroll through the red-brick streets in Colonial Williamsburg, pausing to peek into the 18th century-inspired shops and markets that line the street. Photography courtesy of Visit Williamsburg
Throughout the year, interpreters fill the streets of Colonial Williamsburg, helping to bring its history alive to modern visitors. Photography courtesy of Visit Williamsburg
There are few towns where you can stroll the streets alongside interpreters dressed in colonial attire. They make downtown Williamsburg tick: Foreign diplomats roam the streets, merchants sell fine wares at the shops, and blacksmiths hammer horseshoes for the steeds that pull carriages through the streets. You might even spot familiar names like Martha Washington and Thomas Jefferson conversing.
Set yourself up for a day of sightseeing with coffee and a tasty treat from The Bake Shop, a collegiate space at the edge of William & Mary’s campus. From there, you can walk to the bustling Duke of Gloucester Street, where colonial meets commercial between the old-timey shops and taverns. Marvel at traditional handicrafts like leather, woodworking, and ceramic pieces at the Prentis Store or John Greenhow Store, and strike up a conversation with any of the costumed interpreters in the street. Not only do they adopt a fitting accent for whomever they’re portraying (including the native tongue for international characters), but they have extensively studied their histories and will happily share their story with you. Make your way toward sites like the stately Governor’s Palace or the Bray School, the oldest extant building in the country dedicated to the education of Black students.
Take a break from the sun in the shaded grounds behind the Governor’s Palace. Photography courtesy of Visit Williamsburg
When you work up an appetite, lunch at The Cheese Shop is a quintessential Williamsburg experience. Owned and operated by the same family for more than 50 years (and kin of the co-founder of the Blue Point in Duck, North Carolina), their sandwiches are simple by design but allow high-quality ingredients to shine, including their customer-favorite house dressing. Get your order to-go and take it to the grassy pastures for a picnic lunch.
While exploring on your own is plenty fun, a guided carriage ride or walking tour is a fast way to glean fascinating facts and stories about Williamsburg, the founding fathers, and surrounding area from knowledgeable guides.
You can sightsee Colonial Williamsburg by foot or climb into a horse-drawn carriage, led by a knowledgeable guide. Photography courtesy of Visit Williamsburg
For dinner, you can walk to plenty of places right in the heart of the colonial town. You can continue the 18th-century experience at establishments like Christina Campbell’s Tavern, a favorite watering hole of George Washington. Menu items are recovered recipes from past housekeepers, kitchen assistants, and other notable folks (try the fried fish from the personal cookbook of Thomas Jefferson).
If you prefer to dine with a more modern edge, make a reservation at Fat Canary. This New American bistro serves up elevated plates where regional ingredients, like house-made mozzarella and Virginia ham roulade served with walnut pesto, heirloom tomatoes, and balsamic. Save room for the strawberry shortcake with cream cheese frosting, candied pistachios, and graham cracker crumble.
Take your Mobjack Coffee Roasters order to-go to enjoy as you mosey around Historic Yorktown’s pedestrian-friendly streets. Photography courtesy of Visit Williamsburg
Start your day right with a house-baked apple turnover and one of the coffees roasted in-house at Mobjack Coffee Roasters. Housed inside a craftsman-style brick building with teal shutters, this cozy, wood-paneled cafe — complete with fireplaces — is the sort of space you could spend all day (or at least return to for lunch). You can enjoy your treat in the upstairs tearoom or outdoor picnic tables. Then, finish the rest of your coffee while exploring the pedestrian-friendly streets in Historic Yorktown.
“We had a social media influencer come last year, and we were walking on Main Street,” Gucanac recalls. “And she said, ‘Wow, you really have re-created that small town, local vibe,’ and I said, ‘We didn’t re-create it, this is it.’ This village evolved from Revolutionary history to the present day. We’re the next chapter.”
Many of the buildings here are part of Colonial National Historical Park, so they’re managed and leased by the National Park Service. “When you come to Yorktown, there are certain things you have to see. It’s our job as business owners to bridge that gap and make sure things are accessible. We chose this location on purpose,” Gucanac says of Mobjack’s historic space. “We keep our building as an experience in Yorktown that people can visit as an extension of the park.”
Cast your line and take in the view of York River from the Yorktown Fishing Pier. Photography courtesy of Visit Williamsburg
For a comprehensive deep-dive into this history, head to the American Revolution Museum where you can check out artifacts, immersive exhibits, galleries, and more. Or, if you prefer to gain an appreciation of the locale from an early settler’s point of view, board a schooner through Yorktown Sailing Tours and set sail on a breezy cruise around the York River. As the only deep-water port in the southeast during the colonial years, Yorktown is home to around 300 years of history. Cruise past the battlefield, Victory Monument, and Yorktown Beach. If the weather’s nice, you can bring a bathing suit and swing by the beach after you deboard the boat at Riverwalk Landing Pier.
Before you leave, pick up something sweet from Little York Confectionery, located inside the circa-1700 Somerwell House. With a variety of bonbons, homemade ice cream, and artistic chocolates, you’ll find plenty of sweet endings to your time in Historic Yorktown.
Ready to uncover the living history in Virginia’s colonial capital? Click here to learn more about each town and start planning your visit.
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